Modern Allene Chemistry
Norbert Krause, A. Stephen K. Hashmi
Pages, 2 Volumes
First Edition, 2004
This two-volume handbook covers all the important aspects and facts related to this hot topic. With their excellent contributions an international team of outstanding authors highlight the multifarious uses and classes of allenes, making this an indispensable book for every organic chemist.
Historically, allenes have been viewed as a chemical curiosity, and their very existence was doubted. This situation can be explained on the basis of the available methods for structure elucidation, which for a long time were unable to detect this functional group. Some natural products were wrongly thought not to be allenes, or likewise were falsely assigned to this group. At the current point in time, this moiety has been detected in some 150 natural products, and a number of structural assignments have been revised.
To the average chemist, the synthesis of allenes can indeed be akin to witchcraft. Often not covered in lectures, or mentioned solely within the hour spent on stereochemistry, these compounds seem consigned to a shadowy existence. Thus it is surprising to learn how simple the synthesis of allenes really is. The available variations make it possible to prepare them with a high tolerance for other functional groups. As it showcases the most important synthetic routes including enantioselective transformations, along with a number of interesting synthesis examples, this book should finally demystify the preparation of these compounds.
Now, having learned from the first book how to prepare allenes, begs the question of why there is so much interest in this functional group's synthesis. The answer to this question appears in the second book; in fact, they undergo a broad range of reactions. Electrophilic and nucleophilic reactions, as well as radical reactions and a wide variety of cycloadditions, cyclizations, and oxidations all lead to a multitude of structurally diverse possible products. Selectivity is a constant focus, and many of the reactions mentioned as examples illustrate the factors that can be expected to play a role, and how these come together to influence the selectivity.
Anyone with a general interest in these compounds, or who wishes to put the subsequent synthetic reactions of allenes to use, should definitely take a look through the two volumes of Modern Allene Chemistry.
SYNTHESIS OF ALLENES
Synthesis of Allenes by Isomerization Reactions
Metal-Mediated Synthesis of Allenes
Transition-Metal-Catalyzed Synthesis of Allenes
Enantioselective Synthesis of Allenes
SPECIAL CLASSES OF ALLENES
Allenic Hydrocarbons - Preparation and Use in Organic Synthesis
Cyclic Allenes Up to Seven-Membered Rings
Synthesis and Reactions of Allenylmetal Compounds
REACTIONS OF ALLENES
Ionic Additions to Allenes
Fundamentals and Application of Free Radical Addition to Allenes
Cycloadditions of Allenes
Cyclizations of Allenes
Transitions-Metal-Catalyzed Cross-Couplings of Allenes
Transitions-Metal-Catalyzed Cycloisomerizations of Allenes
Transition-Metal-Catalyzed Addition/Cycloaddition of Allenes
Oxidation of Allenes
Allenic Natural Products and Phamaceuticals
Allenes in Natural Product Synthesis